


Esoteric Regret

by JamesLucien



Category: Supernatural
Genre: Anal Sex, Asphyxiation, Copious Amounts of Cum, Demons, Dom/sub, Double Penetration, Duel Cocks, F/M, First Time, Horror, Lust, Monsters, Oral Sex, Outdoor Sex, Painful Sex, Paranormal, Rape, Rough Sex, Supernatural Elements, Vaginal Sex, magick, monsterotica
Language: English
Status: Completed
Published: 2014-05-30
Updated: 2014-05-30
Packaged: 2018-01-27 15:40:52
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 3,501
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1715885
Author URL: https://archiveofourown.org/users/JamesLucien/pseuds/JamesLucien
Summary: <blockquote class="userstuff">
              <p>Esoteric Regret is a horror erotica novella fanfic that takes place in the same world as the Supernatural TV series.</p><p>While her parents are away for the night, a nerdy loner infatuated with the occult, evokes a powerful demon without the proper binding spell, unleashing the vicious malignance of hell upon herself.</p><p>The pornstar, Dillion Harper, is the physical inspiration for this original character. A Google image search will provide visual aid to those who desire it.</p><p>Please note I have only watched the first five seasons, therefore this story does not take into consideration anything beyond that point in the canon.</p>
            </blockquote>





	Esoteric Regret

I’m Imogen Meriwether, a sixteen-year-old book nerd, and there’s no denying it. Reading is my passion. Fiction and non-fiction. Specifically, anything to do with the mysterious and secret. I have the entire Carver Edlund Supernatural series and have read them multiple times. I’ve also read every Wincest fanfic on morethanbrothers.net. If Sam and Dean were real, I’d offer either one or both my virginity in a heartbeat. The thought of the two of them sharing me, kissing and caressing and filling me, is enough to make me cream my panties!

My father’s the Chief Surgeon at a Trauma Center and my mother’s a Realtor for a Luxury Real Estate company. So we live in a huge house where the maid and gardener spend more time than they do. Although I rarely see them, they still manage to control my life to a nauseating degree. They force me to go to an all-girls private school where everyone’s a snob, a closet drug addict, or both. And because I have no friends, I spend my lunch period in the expansive library, the only real benefit of attending the school. During a random fire drill last week, I managed to sneak into the restricted area and stole an archaic book. An actual grimoire!

I read it cover to cover twice. No small feat since it’s written in Latin. I had to type it all into an online translator. But now I’m ready to attempt a summoning ritual. If I’m successful, I plan to use the spirit to direct a hot stud with a love of books my way.

I often daydream about a sexy pool boy rubbing me down before pleasuring me, a new neighbor jogging by as I come home from school and following me up to my bedroom for steamy sex, and even a thief breaking in when I’m alone and having his way with me.

I know it’s stupid, but I’m dressed up for the occasion. In an outfit my parents would never approve of. My brunet hair is tied into pigtails with black bows, and my big blue eyes are accentuated by black eyeliner, behind my black-framed glasses balancing on the bridge of my button nose. I’m wearing a sleeveless pink blouse to emphasize my pink lips, pink and black plaid miniskirt that flaunts my slim thighs, along with matching black ruffled choker, opera-length gloves, and thigh-high stockings. A silver pentacle hangs in the cleavage between my C-cups as well. If it’s possible to be a nerd and a goth at once, that’s me.

My parent’s friends describe me as cute and adorable, but they never bring around any boys close to my age. I’m buxom thanks to my curvy mother, fit since tennis is a daily requirement at my school, and lithe because I’ve been in a ballet academy since I was five due to my father’s insistence.

My parents are away for the night at a hospital charity event, so I’ve got the house to myself. Yippee!

With moonlight shining through the glass patio doors into the dining room, I push the dinner table and chairs against the wall and roll up the oriental rug. Severus, my fluffy black cat, watches me from atop my mother’s curio cabinet, as I carefully pour sea salt in the form of a large pentacle. Place a round mirror I’ve spray-painted black within the center. Then set black candles at the five points and light them.

After switching off the lights, I sit lotus facing the patio doors, open the ancient book in my lap, and turn to the evocation. Inhaling a deep breath, I hold it a moment and exhale slowly to focus my mind. Magick requires razor-sharp intention. Then I do my best to pronounce the Latin correctly and clearly at a good volume.

While I read the temperature rises until perspiration sweeps across my brow, yet cold shivers surge up and down my spine as I notice the shadows elongating and twisting. As I state the closing line of the conjuring rite, the room darkens as if clouds are blocking the moon, though the candlelight diminishes as well. Severus rumbles a low hissing grow with his ears back and his spine arched, then leaps off the curio cabinet and flees. An electric sensation flows over me in prickling waves. The room becomes heavy like the air is taking on weight. A ringing begins to buzz in my ears, growing louder and louder, until my drums pop and the painted mirror spiderwebs. Black smoke seeps through the cracks, only wisps at first, but soon it pours forth and swirls into the air, bringing with it the stench of death and decay. It forms into the shape of a person!

I stand up in amazement, my eyes wide, my heart pounding, my mind racing in disbelief, and a blinding crimson light knocks me to the floor. When my eyes readjust, a muscular naked man is standing atop the fractured mirror. He appears to be a perfect conglomerate of every fantasy I’ve ever had, except his eyes are a lurid yellow.

I scoop up the book of spells and find the binding incantation. As I read I rise to my feet, and the nude man closes his shocking eyes, his every muscle flexing until I finish.

His voice is deep but soothing. “My power is yours. Break the circle so I may attend to your desires.”

With a black stocking-clad foot, I sweep a line through the salt, releasing the spirit that has manifested a body.

He marches out of the broken pentacle, and a sinister smile splits his handsome face. “Your binding spell... It was written for a spirit.” He looks me up and down, sultrily licking his lips. “Your evocation spell, however, was not.”

The grimoire falls from my trembling hands as I gasp. I shake my head in terrible realization. “No! No! No!”

He nods his head. “Oh yes, yes, yes my child.”

I beg. “Please, please return to where you came from!”

He throws back his head in an explosion of laughter that mutates into a hideous roar so intense it shatters the patio doors, the windows, and the curio cabinet glass. Thankfully my lenses are shatterproof.

I reach for the dropped book, hoping to use a banishing spell, but the demon kicks it away.

Stepping backward, I bump into the table, as I watch him transform!

Obsidian horns sprout from his forehead. Vampiric fangs bulge from his darkening lips. A black forked-tongue slithers from his smirking mouth. A second pair of arms extends from his sides. Onyx talons jut from his fingertips. His skin morphs into the scarlet scales of a snake, yet bushy red hair spreads over his barrel chest, forearms, and from his knees down to his cloven hoofs. His muscles triple in size as he grows wider and taller, towering over me. An arrowhead tail shoots from his tailbone and wraps tight around my waist. He stretches his four arms outward and black leather wings spread from his back, filling the room, before folding in. And his mighty manhood, black as midnight, doubles in girth and length as it rises to full salute.

His voice is now gravelly and harsh. “Before I do with you as I please, I wish to imbibe the sweet nectar of this earthly realm. Where is your alcohol?”

With a shaking hand, I point to the liquor cabinet, and stammer. “M-m-my father keeps it locked up.”

I’m lifted off my feet by his gripping tail, and one of his wings extends to wrap around me. He stomps across the room to the cabinet, the floorboards creaking under his weight, and tears the doors off their hinges with ease. Unsealing a bottle of Johnnie Walker Blue Label scotch, he gulps it down in its entirely, while opening another bottle with his second set of hands, and then guzzles half of it down, before turning his head toward me. “Drink my child. You will be thankful you did.” And he presses the mouth of the bottle to my lips, pouring the whiskey down my throat as I cough, the liquor spilling all down my neck and blouse within the cocoon of his wing.

It burns going down, and a tingling warmth blooms in my belly and spreads throughout my body, diluting my mind-numbing fear and numbing my senses. I’ve never drunk alcohol before.

Uncoiling his wing, I plop to the floor landing on my knees, the room spinning around me. His prehensile tail slides up my soaked blouse, and rips forward, popping all my buttons. Using his tail, he slips off my shirt and tosses it aside before tearing off my bra, liberating my breasts, bikini tan lines visible in the dim candlelight.

His upper hands grope at my bosoms, squeezing and mashing them roughly, as his lower set anchor my arms at my sides, while his massive pulsating member waves in my face, taunting me with what is sure to come next.

I attempt to pull my arms free, but I can’t even budge them. He’s too strong! “No! No! No! Get off me! Let me go!”

With a violent twist of his hips, he smacks me across the mouth with his colossal cock as I utter a pained gasp of surprise, my glasses sliding to the tip of my nose and my bottom lip busting open, blood dribbling down my chin.

As I begin to shed tears he palms the back of my head with his upper hands, his lower hands now harshly groping my breasts, and he thrusts his pelvis hard, shoving his engorged prick into my screaming mouth, stretching my lips wide. I pound and punch my fists on his arms and thighs, desperately fighting back as he rolls his hips, fucking my mouth as he groans, the fat head of his beast jabbing the back of my throat, again and again and again.

When he pulls out I pant for air, and he lifts his heavy scrotum and rests it on my face. He growls, “Lick my balls you dumb little bitch, or I’ll cock slap you bloody.”

Terrified of another smack, I lap at his scaly balls until my tongue is dry as he gropes my bottom as well as my bosoms.

As I’m gathering saliva to moisten my parched tongue, he coils his tail around my neck, turns around, spreads his muscular cheeks, and pulls my face between them. “Now eat my asshole, you stupid whore.”

I reluctantly dab my tongue at his black bud, and it opens and I balk.

His tail tightens and he grumbles. “Stick it in there deep or you’ll be sorry.”

I do as he demands, poking my tongue all the way in, and swirl it around and around as he moans. It tastes like brimstone!

Eventually, he pulls me from his cheeks and spins around. “I wanna taste my ass on your little mouth.” He lifts me into the air by the throat and my tongue sticks out automatically as I choke. He sucks my tongue with his drooling lips as I kick and thrash.

When I’m too weak to writhe, darkness creeping into my vision, he drops me. I cough and gasp for oxygen as I rub my throat.

Before I’ve recovered, he clutches my pigtails and shoves his mammoth cock into my sobbing mouth with a brutal lunge. Pulling back, all but the head remaining between my lips, he thrusts hard, plunging his behemoth into my throat, straining the limits of my esophagus, threatening to split it open.

I choke and gag as I rake and claw at his rigid abs in a frantic struggle, while he savagely assaults my throat, forcing his monolithic monster deeper and deeper, until his heavy balls are slapping my chin. I tug on his scrotum with all my strength, resisting with everything I’ve got, as he fucks my throat raw with angry grunts, but to no avail. It’s obvious by his malicious smile that he relishes my fruitless efforts to resist him, and the daunting realization breaks my natural volition for self-preservation.

My fortitude forsaking me, my will to live perished, I cease fighting and go limp, my arms dangling at my sides, my crying eyes staring blankly, allowing him to plunge my throat freely, like a flaccid sex doll, a mere toy, a foolish girl who rose a demon from hell.

When I fail to feed his need for resistance, he lashes my breasts with his tail, stinging my tender flesh, but I do not give into his yearning for opposition, and in frustration he pillages my throat with even more brutality, yanking my pigtails as he lunges his hips, my neck in danger of snapping.

I’m on the cusp of blacking out, my consciousness fading, when he roars and scorching spunk overfills my stomach, backs up my sore throat into my mouth and sinuses, running from my nose and pouring from my lips. It cascades down my chin splashing from my breasts to the floor, and he pulls out spraying more steaming splooge over my face, completely coating my glasses.

I cough and sneeze and then I heave, puking an abhorrent amount of his goop all over myself.

Squeezing my hot goo covered bosoms together, he thrusts his throbbing prick between them, tittie fucking me as I continue to purge his foul seed from my wrenching stomach, adding more lubricant to my chest.

When I can’t retch anymore, I smear the slime coated lenses of my glasses with my gloves enough to see. Dancing with the desire of him taking my life, I glare up at the demon and spit the last mouthful of semen into his devilish face. I croak, “Fuck you!”

He smirks, grasps my by the waist, and heaves me into the air, planting me on his broad shoulders. With his sharp fangs, he rives through my panties, exposing my pink slit. Then laps at my sensitive button with his forked tongue as I quiver and moan, gripping his obsidian horns for balance as I kick wildly at his back.

I’m tormented by the astounding ecstasy of his slithering snake tongue, amping my urgency for release higher and higher. Fiercely battling my ascending orgasm, I force it back with all my willpower until it overpowers me in an earthshaking detonation of carnal bliss that causes me to scream and quake in a delirium of rapture.

The demon tosses me down on the table and pleasant aftershocks cause me to flop weakly like a suffocating fish, as he abandons me for another bottle of expensive alcohol. This is my chance to escape! Get up! Get up!

Regaining my will to live, I roll off the table, falling to the floor with a bang, but he doesn’t seem to care. Crawling on my hands and knees through the salt pentacle, I grab the grimoire. I must banish him! Using the wall as an aid, I climb to my feet. Then with broken glass crunching under my feet, cutting through my stockings and puncturing the calluses of my soles, I stumble onto the patio leaving a trail of scarlet footprints in my wake.

The demon calls after me. “Flee my child so I may chase.”

Fuck! I grit my teeth against the pain of my bleeding feet and hurry down to the pool area. It overlooks an acre of manicured lawn and trimmed hedges, a wooden area beyond masks the perimeter of our property, where there are many places to hide. As a child, I learned every nook and cranny.

Wincing with every step, I hobble around the inground pool, clutching the book of spells to my naked breasts, smearing demonic goop over it. As I reach the stairs to the yard, a flapping of wings grows loud, and I look up to see the demon swooping down at me.

I dive from the top step, but the devil plucks me out of the air, clutching me around the waist, and we fly in a backward arch through the sky as my glasses and the grimoire are lost to the dewy grass below. He spins me around before landing on the water, massive wings spread wide, and spikes my virgin cleft on his gargantuan pike. I wail in agony to the heavens, but no angel replies to my tortured cries.

His onyx talons dig into my hips and waist as he thrusts his pelvis, slapping my cheeks hard and fast, bouncing and jiggling my breasts, as I tear and yank at his bushy red chest hair, squealing in misery and horror as he plunders my taut sheath with his mighty spear, over and over again.

Soon the water roils and boils, steaming mist whirling in little cyclones over the surface, yet it remains cool to the touch of my thrashing feet bleeding into the pool.

When I can’t hold it off any longer, an unholy climax seizes me, wracking my body with jubilant euphoria, and in response, the demon’s megalith erupts inside me like a geyser. The incredible force of his ejaculation tosses me backward into the water, plunging beneath the churning surface. Swim! Swim! Go! Go! I gotta escape!

I kick and paddle to the edge, surface with a gasp, and pull myself from the pool. Dripping wet, I scurry down the stairs to the yard, and scoop up the grimoire and my glasses, before rushing for the woods. Run! Run! I gotta hide!

I pant and hold my aching side as I make it into the trees. But then I’m plowed into the grass by the weight of the demon landing atop me with a bellow of scorn.

I scream, “Please! Please! No more! No more!”

His hot breath tickles my ear and causes the hairs on my neck to raise as he whispers. “But I’m having so much fun. I can’t stop yet. I haven’t even plundered your tiny asshole.”

Shivering in dread, I plead, “Please! Not my ass! Please!”

He growls, “Yes, beg me!”

“Please! Please! Please! _Pleeeease!_ ”

I shriek in harrowing excruciation as he stabs his nephilim between my cheeks, tearing me open as he borrows deep into my ass. I claw at the earth, pulling up clumps of soil and snapping tree roots, frantically trying to crawl away as he pounds me into the dirt. I grunt through gnashing teeth, tears streaming down my face, writhing and thrashing in agony as he pulverizes my backside, bucking his hips like a wild stallion in fear of capture.

When my grunting screams become raspy cries due to my hoarse throat, he pulls out, giving me a moment of respite. Panting, I look back over my shoulder and my eyes go wide as he sprouts a second monstrous erection.

Gripping me behind the knees with his lower set of hands, he pulls them up to my sides into a frog-legged position. With his upper hands, he grasps my shoulders and then forges into both my tender orifices at once.

With ravenous groans and morbid laughter, he rams my pussy and ass, harder and harder. I screech at the top of my lungs, my throat ragged, my every muscle cramping in pain, as the surrounding grass and foliage wilts, worms and centipedes bleed from the soil, and my heart blackens, my spirit withers and my soul is corrupted by darkness.

Finally, he roars and pumps my bleeding holes overflowing with burning jizzum, pulls out, sprays more up my back, flips me over, and douses the front of me as well.

The satanic creature rises with a satisfied smirk as he shrinks and shifts back into my perfect sexual fantasy. “What is your name, my child?”

Literally unable to resist, I answer, “Imogen Meriwether.”

“Imogen, I’m Azazel.” He reaches out a palm.

His name is so familiar! But my mind is too frazzled at the moment to recall from where.

I take his outstretched hand and a warm tremor flows through me, dissolving all my pains as my wounds are healed. Even the shards of glass expel from my soles.

He pulls me to my feet, his goo oozing down me. “You’re a virgin again, and also bound to me. Spirit and soul. You are my daughter and I am your master for eternity. But do not fret. I’m going to give you what you desire. The Winchester boys. You’ll have them both. And then their souls will be mine.”

My mind reels in shock and revelation. Sam and Dean are real! And I resurrected their mother’s murderer!

The porch lights illuminate the yard. “My parents are home!”

“I will handle your mother, while you seduce your father.”

My stomach wrings with revulsion. “Master, please clarify.”

“You must hone your skills in preparation for the Winchesters. I’ve given you powers of enchantment. You will enthrall your father into spilling his seed upon you and within you.”

I swallow hard and whisper with heart-rending sorrow. “Yes, Master.”


End file.
